Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides

[Image: see text] A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described. This transformation allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereose...

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Autores principales: Vázquez-Galiñanes, Nuria, Velo-Heleno, Isabel, Fañanás-Mastral, Martín
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664487/
https://www.ncbi.nlm.nih.gov/pubmed/36327136
http://dx.doi.org/10.1021/acs.orglett.2c03390
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author Vázquez-Galiñanes, Nuria
Velo-Heleno, Isabel
Fañanás-Mastral, Martín
author_facet Vázquez-Galiñanes, Nuria
Velo-Heleno, Isabel
Fañanás-Mastral, Martín
author_sort Vázquez-Galiñanes, Nuria
collection PubMed
description [Image: see text] A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described. This transformation allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These two functionalities provide these products with highly versatile reactivity, as shown by their stereocontrolled conversion into cyclic boron compounds and polyenes.
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spelling pubmed-96644872022-11-15 Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides Vázquez-Galiñanes, Nuria Velo-Heleno, Isabel Fañanás-Mastral, Martín Org Lett [Image: see text] A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described. This transformation allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These two functionalities provide these products with highly versatile reactivity, as shown by their stereocontrolled conversion into cyclic boron compounds and polyenes. American Chemical Society 2022-11-03 2022-11-11 /pmc/articles/PMC9664487/ /pubmed/36327136 http://dx.doi.org/10.1021/acs.orglett.2c03390 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Vázquez-Galiñanes, Nuria
Velo-Heleno, Isabel
Fañanás-Mastral, Martín
Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title_full Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title_fullStr Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title_full_unstemmed Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title_short Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B(2)pin(2) and Vinyl Epoxides
title_sort bifunctional skipped dienes through cu/pd-catalyzed allylboration of alkynes with b(2)pin(2) and vinyl epoxides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664487/
https://www.ncbi.nlm.nih.gov/pubmed/36327136
http://dx.doi.org/10.1021/acs.orglett.2c03390
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